There are few things less pleasant than that sinking feeling you experience after accidentally sending a very private, personal e-mail to an unintended recipient (or worse, recipients) — one fatal click can make the next day at work incredibly awkward. Gmail has an “unsend” feature, but it’s only available for a brief window of time and, of course, restricted to e-mails that travel through Google servers. What if you don’t realize your mistake until later, or what if you’re an Outlook user? UnSend.it is here to help. Ostensibly.
UnSend.it debuted in beta to little fanfare earlier this week, but seems to be picking up steam — the waiting list has grown to 76 eager folks since yesterday. Color me unsurprised. The conceit of UnSend.it, the power to erase every vestige of an ill-conceived message after the fact, is an attractive one. Sadly, though, UnSend.it isn’t the magic service we’ve all been waiting for, and there are several reasons for that.
The protocols may have changed since programmer Ray Tomlinson sent the first e-mail in 1971, but the underlying principle hasn’t: e-mail the digital equivalent of the handwritten letter. We’re all aware that the text of e-mails, like envelopes delivered by the post office, can’t be changed or retracted once sent. But the images, at least in the case of email, can.
Pictures embedded in e-mails are fetched from a server remotely, a function UnSend.it takes full advantage of. When you send an e-mail through the service, you’re really creating an image file of whatever text you’ve typed – unSend.it converts your message into a JPEG and embeds it in the e-mail body. That allows you, of course, to “unsend” a message by generating a new image. UnSend.it takes the concept to its logical limit, allowing you to edit the message, too. And the service even injects tracking code into the images, allowing you to see whether or not they’ve been read.
The security implications of e-mail images aside, UnSend.it just won’t cut it for most day-to-day messaging. Many Outlook and Gmail inboxes are set to block images by default, a configuration many recipients won’t be willing or able to toggle. And sending image-based e-mails instead of text, not to mention e-mails with a conspicous, unremovable signature advertising UnSend.it as “Regret-Free Emailing,” might make your motives understandably suspect.
And then there’s the interface. The UnSend.it dashboard is the definition of barebones, with nothing more than a tab each for sent messages, “alerts,” and the e-mail writer. Want to attach a file or CC someone? You’re absolutely out of luck. Beyond basic formatting and image insertion via URL, you won’t be doing much serious composing.
In UnSend.it’s defense, using the website shouldn’t technically be a requirement. A step-by-step guide outlines how to send e-mail from a Gmail account through UnSend.it servers, but I wasn’t able to get it working after multiple attempts.
Even when all the kinks have been worked out, though, it’s tough to imagine relying on UnSend.it for all messaging. It’s too insecure, too obvious, and, for now, too much of a bother. The idea is an undeniably good one, if not very original, but UnSend.it doesn’t quite manage to live up to the promise.
Until the emergence of a fully functional “unsending” service, I suggest triple-checking the sender field on your next particularly sensitive e-mail for good measure.
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